If he's thinking of leaving the military, I'm guessing he's around 45. A life annuity for a 45-year old with a $4,000/year inflation-adjusted benefit would cost about $110,000 from an insurance company.

If he leaves at 27 years, he'll be 49, if he stays til 30 years, he'd be 52. Does that change the cost much?

</snip>

A bit. An annuity costs less if you buy it when you're older. It's probably worth about $100,000 at age 52 and $105,000 at age 49.

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